Synthesis and characterization of IPrMe-containing silver(I), gold(I) and gold(III) complexes

Abstract

The compounds 4,5-dimethyl-N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene silver chloride [AgCl(IPr^Me)] 3 and 4,5-dimethyl-N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene gold(I) chloride [AuCl(IPr^Me)] 4 have been synthesized. The attempted synthesis of the corresponding 4,5-dimethyl-N,N′-bis(2,6-diisopropylphenyl)imidazol-2-ylidene gold(III) chloride by oxidative addition of chlorine gas on 4 allowed for the formation of the expected complex, concomitantly with 6, resulting from a chlorination of a methyl group situated in the backbone of the NHC (N-heterocyclic carbene). Additionally, the buried volume %V_bur of the IPr^Me ligand in [AgCl(IPr^Me)] 3 and [AuCl(IPr^Me)] 4 complexes was calculated and compared to %V_bur of more classical NHCs. This quantification of the steric hinderance of the IPr^Me ligand reveals the influence of the substituent modulation in the backbone of NHCs.